Background: The organic sector is often suggested as a lever with a potential for contributing to the three dimensions of sustainability: social, environmental, and economic. This study aims to investigate selected organic initiatives and organic food sectors in different locations, such as capital cities, rural areas, and the bio-district in SysOrg project consortium, in the Warsaw municipality in Poland, North Hessia region in Germany, Cilento bio-district in Italy, Kenitra province in Morocco, and Copenhagen municipality in Denmark to uncover the diverse drivers, barriers, and entry points to enable a transformation process to resilient and sustainable organic food systems. Methods: Following the methodology of the SysOrg project, this study relied on the following mixed data collection methods: quantitative (a household survey distributed among citizens) and qualitative (semi-structured interviews with organized initiatives). Results: The results demonstrate that, despite being in different stages of development in the investigated territories, the organic sector is challenged by similar barriers (e.g., undeveloped market, regulatory/budgetary constraints, and lack of knowledge and awareness) and benefits from analogous drivers (e.g., awareness and education, community support, and incentives). Conclusions: Those similarities, but also analyses of their differences and origins, allowed us to establish critical entry points for the development of a sustainable organic food system, e.g., promoting organics through a top-down approach, providing training and education, reducing information delay, popularizing negative feedback, strengthening the effectiveness of a given incentives scheme by tailored nudging mechanisms, establishing country/regional specific traditional frames, making the system more inclusive, building organic communities, and awareness-building.